


Get out of jail for free-card

by schrijverr



Category: Supernatural
Genre: Arrested Dean Winchester, Gen, Law Enforcement, Pre-Canon, Pre-Season/Series 01, Stanford Era (Supernatural), Stanford Student Sam Winchester
Language: English
Status: Completed
Published: 2020-09-27
Updated: 2020-09-27
Packaged: 2021-03-07 19:47:48
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,516
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26683186
Author URL: https://archiveofourown.org/users/schrijverr/pseuds/schrijverr
Summary: Stanford-era Sam gets a call from Dean, who has been arrested and needs him to bust him out. Jess insists on coming with him and is in for a bit of a surprise with the revelations that come with meeting Dean.
Relationships: Dean Winchester & Sam Winchester, Jessica Moore/Sam Winchester
Comments: 6
Kudos: 157





	Get out of jail for free-card

**Author's Note:**

> You can also find this on my tumblr, which is @schrijverr as well

It was Friday, which meant drinking and having fun for Sam and his friends. Jess was just asking what everyone wanted to drink when a phone rang. It took a few seconds before Sam realized it was his. He shot a confused look to his friends and picked up: “Uh, hello, this is Sam Winchester speaking?”

“Sammy, thank God.”, came Deans voice from the other side.

Shocked Sam said: “Dean?”

“Yeah, it's me, already forgotten the sound of my beautiful voice?” Sam practically heard the smirk in that statement.

He couldn't help the bitch face as he answered: “How could I ever forget that annoying sound. But why the fuck are you calling me?”

Tom raised his brows to Jess who gave him a confused look back, Sam wasn't known to swear and neither had ever heard of this Dean person. They were pulled back to the phone call when Sam exclaimed: “What do you mean you got arrested.”

The comment got Jess to give him A Look, so Sam told Dean: “Wait a sec, gotta move.”

Then he waved at them and said: “Sorry have to take this, you guys go and start the movie.”

Jess frowned, but Sam didn't notice as he was saying: “Yes, Dean, movie night, normal people do that sort of thing on Friday. And don't call me Samantha. Now why are you arrested again?”

“Grave desecration, not really a good excuse for that, you know.” Dean said.

Sam rubbed his forehead and asked: “And why is this my problem again?”

“Dad's in Ohio together with Bobby, a demon, he wouldn't take me, so I got an easy salt 'n burn in San Francisco, but I got busted.” Dean replied.

“Do you need bail money or do you need to be saved?” Sam asked with a tired voice.

“I'm no Disney Princess, dude.” Dean said, “Psh, getting saved. But no, no bail for me, just heard you're pre-law now.”

Sam sighed as he read between the lines, Dean needed Sam to bust him out of a holding cell. He said: “Tell them you called a lawyer and won't do anything until he's there. And what name are you going by right now?”

“Phil Rudd.” Dean said, of course it was a rock star name.

He sighed again and said: “I’ll be there in 50.”

“Thank you, Sammy.”

“It’s Sam.” Sam bitched back, then he hung up and snagged a tie out of his closet along with a dress shirt.

He walked back into the room, where no one had started the movie and everyone was ready to pounce him with questions. “Who’s Dean?” Jess asked.

“And why is he arrested.” Tom added.

Sam grimaced and awkwardly said: “He's my brother, so I'm gonna go pick him up at the police station.”

“And why is he arrested?” Jess asked with an intense look.

“Uhhh,” Sam looked away with an embarrassed flush and said: “Grave desecration.”

“He did what!” Jess exclaimed, “That's terrible! Why would he do that?”

“He has his reasons.” Sam said curtly, then he realized that that didn't help the situation, so he went on: “Look he's a good guy, honestly, just a shitty past that he didn't shake off as well as I did. If you'd meet him, you would know.”

“Then take me with you.” Jess demanded.

Their friends had been watching the discussion like it was a tennis match and in the tense silence that followed they kept their eyes on Sam. Sam, who was having a small crises. On one hand he didn't want to fuck up his relationship with Jessica because he didn't take her with him, but on the other hand he also didn't want to fuck it up because he was busting his brother out, illegally.

When the silence dragged on Jess said: “I’m not letting this go, Samuel, take me with you or this is over.”

And that made the decision for him, he said: “Okay, let’s go, I told him I'd be there as fast as I could.”

~

The ride was silent and tense for the first 15 minutes, then Jess said: “I don’t want to meet your brother with just a bad image, so what's your best memory?”

“Huh?” Sam asked dumbly.

“What's your best memory of you and Dean?”

Sam smiled softly and said: “Where do I start? God, he was always there for me for a start, according to him my first words were “Bean” in an attempt to say his name, he says he cried.”

He thought some more before saying: “I know it sounds weird, but with Dad almost always gone and mom dead, while constantly on the road, Dean was my everything. He was my brother, best friend and mom all rolled into one. We were SamnDean, no spaces between us.”

Jess shot him a look, but didn’t say anything and he didn’t either, he just looked at the road and thought back to the times were this sight was his daily view, just from the backseat, with two pairs of shoulders and two heads blocking his view.

~

When they arrived Sam turned to Jess and said: “I need you to stay in the car, please?”

Then he got out of his flannel and buttoned up the dress shirt and put on the tie. Jess frowned at that and asked: “Why? What's going on, Sam?”

“It’s kinda hard to explain, but you have to believe me when I say I hate this as much as you will. Just stay in the car. Me and Dean will be here in a few minutes.” He gave her his best puppy eyes and she relented with an “I don’t like this.”

He gave her a peck on the cheek and said: “I don’t either. See you in a bit.”

Then he was out the car and walking into the station.

Half of the scam was the confidence, so Sam strutted up to the front desk and said: “I’m John Singer, I'm here for Phil Rudd.”

The lady gave him a one over and raised a brow. He knew he was still wearing his shaggy shoes and jeans, plus he looked very young. So he kinds dropped the confidence a bit and said: “I’m just the intern, but my boss, Simon Wright, is out of town, so I’m taking the calls right now.”

A look or pity showed up on the ladies face as she said: “Didn’t expect a call this late, did ya?”

He nodded and said: “I haven’t done this before, sorry, could you point me in the right direction?”

She smiled and quickly walked him through what was expected of him. He thanked her profusely as he walked away.

~

Dean greeted him with a smirk and said: “Hey, man, what’s the plan?”

Sam gave him a bitch face and said: “I’m risking a lot by being here, so don’t try anything, okay? Jess is waiting in the car, so lets make this quick.”

“Wait a minute. Who’s Jess?” Dean said.

“My girlfriend, now pay attention we can talk later.” Sam said.

Dean whistled impressed, but stayed quiet while Sam explained: “They think I’m an intern, so a newbie. You are going to punch me and then use this time window of no surveillance you've created to escape and hide in the back of Jess’s car, okay? It’s the blue crappy Honda.”

Dean chuckled, but nodded. He got ready to punch but Sam held up his hand and quickly sent Jess a text: ‘Dean will join you in the car shortly, don't say anything to anyone. See you in a few.’

Then he allowed Dean to punch him. He waited until Dean was out the window before he yelled: “Help! He punched me and he's gone!”

Soon the whole room was filled with police. His statement was taken and he was checked over, but after 15 minutes they'd let him go while he gave them Bobby's number for if they wanted more info.  
On his way out he texted Bobby about it with a side note not to tell Dad, while he ignored Jessica's messages about how this wasn’t funny.

He got into the car and was immediately slapped by an angry Jess. He looked to Dean who was lying on the back seat to stay out of sight, but he just shot him a ‘hey-don't-look-at-me-dude-this-is-your-problem’ look.

When he said nothing she said: “What took you so long?”

He told her the truth: “They still needed my statement.”

She looked even more angry and said: “Then why is he telling me you busted him out. Illegally!”

He whipped around to give Dean a look and said: “Because he is an idiot.”

“Hey! You brought her with you and told her about your plan. I thought she knew, don’t blame me!” Dean defended himself.

“Why would she know?” Sam said frustrated.

“I don’t know, maybe because she is here and you texted her your plan?”

“God, this is just like Seibert.” Sam gave him an angry look.

Dean got angry as well and loudly replied: “How is this anything like Seibert?”

“Your lack of filter almost fucked me over that’s how.” Sam had a full on bitch face now.

“I told you back then that a twelve-year-old isn’t as convincing as an crying ‘help me I’m lost kid’ than an eight-year-old.”

“And I told you that someone smaller was better for sneaking around, you’re lucky they caught me after I had given dad the keys.”

“I was trying to buy you time, which was my task in the plan.”

“And telling them I was there seemed smart when my task was to remain unseen?”

With every comment their voices got louder and angrier, but before the fight could escalate any further Jess cut in: “What are you even talking about?”

“1991, we were staying in Seibert, but Dad got arrested.” Dean began.

Sam interrupted: “Since when are you such a sharer?”

“Since I’m trying to save your relationship here dude. Look at her, she wants the truth lets give it to her.” Dean shot back.

Sam looked at Jess, who he saw was siding with Dean on the subject. He crossed his arms and muttered: “Like that isn’t gonna ruin everything.”

Then he started up the car and said: “I’m dropping you off at your car hopefully you haven’t lost that too.”

“No, baby is still at my motel, Civic Center Inn, you can drop me there.” Dean said, Jess marveled at how quickly the two calmed down, then Dean turned back to her and said: “So, 1991, Seibert Colorado. Dad had gotten arrested, this wasn’t the first time, so me and Sammy go and bust him out.”

“It’s Sam.”

“Yeah, whatever. So, my plan was that he goes in and acts like he’s lost, creating a diversion for me so that I can sneak dad the keys of his cell.” Dean explained, “Except Sam didn’t agree with that, said I had to play lost, because he was smaller and therefore would be able to sneak better.”

“Which is true.” Sam commented.

“No, it’s not, because it almost went wrong.” Dean jibed.

“And that was your fault.” Sam said.

“No, it’s wasn’t.” Dean started up the discussion again.

Jess just wanted to know what had happened, so she interrupted: “Let it go, both of you.”

“Sorry.” Sam said immediately.

Dean coughed, but Jess was certain she heard “Whipped”, Sam probably did too, because his lips tightened, but he didn’t say a thing. 

Dean went on: “Anyway, I go in and start crying telling them I’m lost and it does create a diversion, but not long enough, so I also tell them I lost my younger brother while I was supposed to be watching him. That does work, a small child is lost, so everyone there starts looking and it the end they find him. He tells them he was looking for the bathroom and wondered away and we get dropped off at a random house, which we tell them is ours. Then we walk to the motel where our father joins us shortly after.”

“We skipped town that night.” Sam finished.

Jess sat quietly for a second as she takes everything in, finally she said: “I’m sorry, Sam, that sounds horrible.”

Sam just shrugged and said: “I’ve never known different, so I never missed it. I’ve been helping in illegal scams since I was three or something. That’s just life.”

“Not that he ever liked it.” Dean felt the need to insert himself into the conversation, “He and dad were always fighting.”

Sam rolled his eyes and said: “Yeah, he didn’t want me to go to college and get a normal life, sorry for wanting to be like everyone else.”

“That didn’t mean you had to fight with him about every little thing, Sam.” Dean said.

Jess sat there awkwardly, feeling that this was a whole other set of issues. She quietly asked: “Is that why you never talk about your family?”

Sam sighed sadly: “Yeah, the last words my dad said to me were: “If you go, don’t come back.” not really heartwarming, is it?”

Dean flopped backwards and said: “Our whole family is shit.”

Sam looked over his shoulder with a surprised look and said: “Didn’t think you would say that.”

Dean shrugged and said: “Doesn’t mean you’re not part of it, Sammy. Just call from time to time, okay? Oh, look there’s the turn.”

Sam turned onto the parking of the motel and Dean got out of the car. Before he slammed the door he said: “Jess, that’s your name right? Yeah, okay, Jess, don’t judge Sam for something he never wanted to be a part of. And Sammy? Sammy you don’t let her go, she’s cool. See you next time, nerd.”

Then he was gone.

Sam sat quietly for a minute then he drove off. They didn’t say anything until they were near San Mateo, then Jess carefully said: “Are you going to call him?”

Sam looked at her and said: “He knows we can’t call each other, he didn’t even give me his number to pretend. We’re never gonna talk again and that’s okay, life happens.”

Jess gave him a pained look, but she didn’t know what to say about it.

Sam asked: “Are we over?”

“No, Sam, we aren’t, just, just be more honest about your life to me, okay?” she said with a sigh.

“Are you gonna tell everyone I broke him out instead of paying a bail that didn’t exist.” Sam asked after a moment of silence.

Jess thought about it for a second. Then she shook her head and told him: “No that’s between you and your brother. I just waited in the car and we had a nice chat about you on the way to his motel, nothing peculiar happened.”

Sam grinned: “What would I do without you?”

Jess smirked back: “Crash and burn.”

~

When Dean broke in to Sams house two years later, he was glad to see that Sam had listened and hadn’t let Jess go.

**Author's Note:**

> This is a bit dated, since it's been in my docs for a log while now, but I still lie the concept and I thought it would be a shame to never post it.
> 
> Anyway Kudos and Comments give me life, so thank you so much for leaving any if you did!


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